title: Synthesis and immunological activity of an oligosaccharide-conjugate as a vaccine candidate against Group A Streptococcus.
abstract: The synthesis and immunogenicity of a tetanus toxoid (TT)-conjugate of the hexasaccharide portion of the cell-wall polysaccharide (CWPS) of the Group A Streptococcus (GAS) is described. The synthesis relies on the reaction of an allyl glycoside of the hexasaccharide with cysteamine, followed by the reaction of the resultant amine with diethyl squarate to give the monoethyl squarate adduct. Subsequent reaction with the lysine ε-amino groups on TT gives the glycoconjugate containing 30 hexasaccharide haptens per TT molecule. The immunogenicity in mice is similar to that obtained with a native CWPS-TT conjugate, validating the glycoconjugate as a vaccine candidate against GAS infections.
authors.affiliation: Department of Chemistry, Guelph University, 50 Stone Road East, Guelph, ON N1G 2W1, Canada.
authors.forename: France-Isabelle
authors.initials: FI
authors.lastname: Auzanneau
authors.forename: Silvia
authors.initials: S
authors.lastname: Borrelli
authors.forename: B Mario
authors.initials: BM
authors.lastname: Pinto
mesh_terms: D000818:Animals; D000917:Antibody Formation; D002240:Carbohydrate Sequence; D005260:Female; D018796:Immunoconjugates / Q000737:chemistry* / Q000276:immunology* / Q000494:pharmacology; D051379:Mice; D008807:Mice, Inbred BALB C; D008969:Molecular Sequence Data; D011135:Polysaccharides, Bacterial / Q000138:chemical synthesis* / Q000276:immunology* / Q000494:pharmacology; D013290:Streptococcal Infections / Q000276:immunology / Q000517:prevention & control; D022541:Streptococcal Vaccines / Q000138:chemical synthesis* / Q000276:immunology* / Q000494:pharmacology; D013745:Tetanus Toxoid / Q000138:chemical synthesis / Q000276:immunology
chemical_list: D018796:Immunoconjugates; D011135:Polysaccharides, Bacterial; D022541:Streptococcal Vaccines; D013745:Tetanus Toxoid
keywords: Cell-wall polysaccharide; Glycoconjugate; Group A Streptococcus; Immunogenicity; Vaccine candidate